5635-50-7

Basic information

• Product Name: HEXESTROL
• Synonyms: MESO-3,4-BIS[4-HYDROXYPHENYL]-HEXANE;DIHYDRODIETHYLSTILBESTROL;HEXOESTROL;HEXOESTROLUM;3,4-BIS-(P-HYDROXYPHENYL)-HEXANE;3,4-DI(P-HYDROXYPHENYL)HEXANE;4,4'-(1,2-DIETHYLETHYLENE)DIPHENOL;3,4-BIS(4-HYDROXYPHENYL)HEXANE
• CAS NO: 5635-50-7
• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.37
• EINECS: 201-518-1
• Mol File: 5635-50-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 399.5°C at 760 mmHg
• Flash Point: 181.6°C
• Appearance: /
• Density: 1.093g/cm³
• Vapor Pressure: 5.92E-07mmHg at 25°C
• Refractive Index: 1.582
• Water Solubility: 11.8mg/L(temperature not stated)
• CAS DataBase Reference: HEXESTROL(CAS DataBase Reference)
• NIST Chemistry Reference: HEXESTROL(5635-50-7)
• EPA Substance Registry System: HEXESTROL(5635-50-7)

Safety Data

• Hazard Codes: T
• Statements: 45
• Safety Statements: 53-45
• RIDADR: 3249
• WGK Germany: 2
• RTECS: SL0560850
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 5635-50-7(Hazardous Substances Data)

Usage

Uses

Vitestrol can be used in methods related to bioactive agents that convert from anions to molecules

Brand name

Synoestrolum.

World Health Organization (WHO)

Hexestrol is a stilbene derivative. See WHO comment for diethylstilbestrol. (Reference: (WHODI) WHO Drug Information, 77.1, 16, 1977)

Purification Methods

Crystallise meso-Hexestero from *benzene or aqueous EtOH (m 185-188o). The meso-dibenzoyl derivative has m 236-237o. The 3RS,4RS(±)-racemate [5776-72-7] crystallises from pet ether, *C6H6/pet ether, Et2O/pet ether, or MeOH/H2O and has m 128-129o . The (±)-dibenzoyl derivative has m 123-124o . The 3R,4R(+)-isomer [26614-21-1] and 3S,4S(-)-isomer [26614-22-2] crystallise from Et2O/pet ether with m 80 -80.5o and have [] D (+) and (-) 17.7o (c 5, EtOH). Their dibenzoyl derivatives have m 116.5o .[Beilstein 6 III 5503, 6 IV 6761.] They have estrogenic activity where optically active forms are more potent and they have antineoplastic activity. [Aboul-Enein et al. Anal Profiles Drug Subst 11 347 1982, J Am Chem Soc 65 4911941.]

InChI:InChI=1/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+

Upstream product

• 13029-44-2 Dienol 
• 56-53-1 diethylstilbestrol 
• 130-80-3 Clinestrol 
• 130-78-9 racem.-3,4-bis-(4-methoxy-phenyl)-hexane 
• 67-64-1 acetone 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 101942-05-6 4.4'-bis-ethoxycarbonyloxy-α.α'-diethyl-trans-stilbene 
• 19115-30-1 1-(4-methoxyphenyl)-2-propyn-1-ol 
• 123-11-5 4-methoxy-benzaldehyde 
• 84234-15-1 bis-[1-(4-hydroxy-phenyl)-propylidene]-hydrazine 
• 70-70-2 4-hydroxypropiophenone 
• 4390-94-7 1,2-bis(4-methoxyphenyl)butanone 

Downstream Products

• 5693-81-2 racem.-3.4-bis-(4t-hydroxy-cyclohexyl-(1r))-hexane 
• 5693-81-2 (+/-)-threo-3-(4c-hydroxy-cyclohexyl-(1r))-4-(4t-hydroxy-cyclohexyl-(1r))-hexane 
• 84-16-2 3,4-bis-(4-hydroxy-phenyl)-hexane 
• 41172-51-4 racem.-3,4-bis-(3-nitro-4-hydroxy-phenyl)-hexane 
• 6033-44-9 racem.-3,4-bis-(4-benzoyloxy-phenyl)-hexane 
• 130-78-9 racem.-3,4-bis-(4-methoxy-phenyl)-hexane 
• 13026-26-1 threo-4-(4-Hydroxyphenyl)-3-(4-methoxyphenyl)-hexane 
• 129579-58-4 threo-3-(Cyclohex-3-en-1-on-4-yl)-4-(4-hydroxyphenyl)-hexane 

Relevant articles and documents

Tetrahydrofuran-mediated radical processes: Stereoselective synthesis of d,l-hexestrol

The highly stereoselective synthesis of d,l-hexestrol (1), an inhibitor of microtubule assembly, is developed by using, as a key step, an intermolecular coupling of Co2(CO)6-complexed propargyl radicals. The latter are generated by novel complementary processes involving an interaction of tetrahydrofuran with Co2 (CO)6-complexed propargyl alcohols and cations. An isomerically pure d,l-μ-η2-[3,4-di(4-methoxyphenyl)-1, 5-hexadiyne]-bis-dicobalthexacarbonyl (d,l-6) is isolated in 69-91% yield with intermolecular coupling reactions exhibiting an excellent chemo-(0.5-7%) and d,l-diastereoselectivity (90-94%). The structure of d,l-6 is determined by X-ray diffraction. The subsequent steps include BBr3-induced demethylation of 4-methoxyaryl groups, demetalation with cerium(IV) ammonium nitrate, and hydrogenation of acetylenic termini affording d,l-hexestrol (1).